Blue-red emitting materials based on a pyrido[2,3- b ]pyrazine backbone: design and tuning of the photophysical, aggregation-induced emission, electrochemical and theoretical properties

Pyrido[2,3- ]pyrazine-based donor-acceptor-donor (D-A-D) molecules were designed by altering donor amines and synthesized using the Buchwald-Hartwig C-N coupling reaction. Further, the tunable opto-electrochemical properties of the dyes were studied in detail. The dye possesses intramolecular charge transfer (ICT) transition (412-485 nm), which marked the D-A architecture and induces a broad range of emissions from blue to red (486-624 nm) in the solution and solid state. Some of the dyes show aggregation-induced emission (AIE) features and formation of nanoparticles in the THF/H O mixture, as confirmed by DLS and FEG-SEM (of 7) analysis. The AIE characteristics indicate its solid/aggregate-state application in organic electronics. The molecules exhibit high thermal stability, low band gap (1.67-2.36 eV) and comparable HOMO (-5.34 to -5.97 eV) and LUMO (-3.61 to -3.70 eV) energy levels with those of reported ambipolar materials. The relationship between the geometrical structure and optoelectronic properties of the dyes, as well as their twisted molecular conformation and small singlet and triplet excitation energy difference (Δ = 0.01-0.23 eV) were analyzed using the DFT/TDDFT method. Thus, potential applications of the dyes are proposed for optoelectronic devices.